2,2-Dimethoxypropane → 1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-nitro-1H-pyrazole

HRID 19191노트

반응식

HRID 19191 반응식
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][C@H:10]([OH:13])[CH2:11][OH:12])[N:5]=1)([O-:3])=[O:2].CO[C:16](OC)([CH3:18])[CH3:17]>CC(C)=O.S(=O)(=O)(O)O>[CH3:17][C:16]1([CH3:18])[O:13][C@@H:10]([CH2:9][N:6]2[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]2)[CH2:11][O:12]1

참가 물질

5

반응물 2

HCID 64952,2-DimethoxypropaneHCID 59344949(S)-3-(3-nitro-1h-pyrazol-1-yl)propane-1,2-diol

생성물 1

HCID 593449571-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-nitro-1H-pyrazole수율 58%

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매HCID 180Acetone용매

실험 절차

A solution of (S)-3-(3-nitro-pyrazol-1-yl)propane-1,2-diol (1.00 g, 5.35 mmol) in acetone (10 mL) was treated with concentrated sulfuric acid (5 drops) and 2,2-dimethoxypropane (3.34 g, 32.09 mmol). The reaction mixture was stirred for 5 h at room temperature. Upon completion of the reaction the mixture was concentrated at reduced pressure and then diluted with ethyl acetate, washed with a saturated sodium bicarbonate solution, a saturated sodium chloride solution and dried over magnesium sulfate The crude product obtained was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 80% ethyl acetate/hexanes) to afford 1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-3-nitro-1H-pyrazole (0.70 g, 58%) as a yellow oil: LR-ES-MS m/z calculated for C9H13N3O4 [M]+ 227, observed 228 [M+H]+.

후처리

  1. customUpon completion of the reaction the mixture
  2. concentrationwas concentrated at reduced pressure
  3. additiondiluted with ethyl acetate
  4. washwashed with a saturated sodium bicarbonate solution
  5. dry with materiala saturated sodium chloride solution and dried over magnesium sulfate The crude product
  6. customobtained
  7. customwas purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 80% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-165d2726afc645c9bc54f13da61ed780
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

반응 노트

불러오는 중…